JPH0415463B2 - - Google Patents
Info
- Publication number
- JPH0415463B2 JPH0415463B2 JP60289539A JP28953985A JPH0415463B2 JP H0415463 B2 JPH0415463 B2 JP H0415463B2 JP 60289539 A JP60289539 A JP 60289539A JP 28953985 A JP28953985 A JP 28953985A JP H0415463 B2 JPH0415463 B2 JP H0415463B2
- Authority
- JP
- Japan
- Prior art keywords
- resin
- composition according
- sensitizer
- diphenylphosphine oxide
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920005989 resin Polymers 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 6
- -1 diazophenacyl Chemical group 0.000 claims description 5
- 229920003986 novolac Polymers 0.000 claims description 5
- YDHGOJBKWDDVPX-UHFFFAOYSA-N (z)-1-(4-tert-butylphenyl)-2-diazonio-2-diphenylphosphorylethenolate Chemical group C1=CC(C(C)(C)C)=CC=C1C([O-])=C([N+]#N)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 YDHGOJBKWDDVPX-UHFFFAOYSA-N 0.000 claims description 2
- IPVAAXCHHBASNB-UHFFFAOYSA-N (z)-2-diazonio-2-diphenylphosphoryl-1-(4-phenylphenyl)ethenolate Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1C([O-])=C([N+]#N)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 IPVAAXCHHBASNB-UHFFFAOYSA-N 0.000 claims description 2
- GXYCJBWPRTZHBY-UHFFFAOYSA-N (z)-2-diazonio-2-diphenylphosphoryl-1-phenylethenolate Chemical group C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=[N+]=[N-])C(=O)C1=CC=CC=C1 GXYCJBWPRTZHBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 2
- MSPODOHAASKUDQ-UHFFFAOYSA-N (z)-2-diazonio-2-diphenylphosphoryl-1-(4-methoxyphenyl)ethenolate Chemical group C1=CC(OC)=CC=C1C(\[O-])=C(/[N+]#N)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MSPODOHAASKUDQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZOERKPRXTZQAOS-UHFFFAOYSA-N (z)-1-(4-chlorophenyl)-2-diazonio-2-diphenylphosphorylethenolate Chemical compound C=1C=C(Cl)C=CC=1C([O-])=C([N+]#N)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 ZOERKPRXTZQAOS-UHFFFAOYSA-N 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/016—Diazonium salts or compounds
- G03F7/0163—Non ionic diazonium compounds, e.g. diazosulphonates; Precursors thereof, e.g. triazenes
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/717,254 US4601969A (en) | 1985-03-28 | 1985-03-28 | High contrast, high resolution deep ultraviolet lithographic resist composition with diazo carbonyl compound having alpha phosphoryl substitution |
| US717254 | 1985-03-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61223837A JPS61223837A (ja) | 1986-10-04 |
| JPH0415463B2 true JPH0415463B2 (enrdf_load_stackoverflow) | 1992-03-18 |
Family
ID=24881303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60289539A Granted JPS61223837A (ja) | 1985-03-28 | 1985-12-24 | リソグラフイ−レジスト |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4601969A (enrdf_load_stackoverflow) |
| EP (1) | EP0195986B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS61223837A (enrdf_load_stackoverflow) |
| CA (1) | CA1221864A (enrdf_load_stackoverflow) |
| DE (1) | DE3662317D1 (enrdf_load_stackoverflow) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0772798B2 (ja) * | 1988-02-17 | 1995-08-02 | テルモ株式会社 | 基板上のパターン形成方法 |
| US5114827A (en) * | 1988-06-28 | 1992-05-19 | Microelectronics Center Of N.C. | Photoresists resistant to oxygen plasmas |
| US4968582A (en) * | 1988-06-28 | 1990-11-06 | Mcnc And University Of Nc At Charlotte | Photoresists resistant to oxygen plasmas |
| DE3900736A1 (de) * | 1989-01-12 | 1990-07-26 | Hoechst Ag | Positiv arbeitendes strahlungsempfindliches gemisch enthaltend einen mehrfunktionellen (alpha)-diazo-(beta)-ketoester, verfahren zu dessen herstellung und strahlungsempfindliches aufzeichnungsmaterial enthaltend dieses gemisch |
| EP0431971B1 (en) * | 1989-12-07 | 1995-07-19 | Kabushiki Kaisha Toshiba | Photosensitive composition and resin-encapsulated semiconductor device |
| DE4014649A1 (de) * | 1990-05-08 | 1991-11-14 | Hoechst Ag | Neue mehrfunktionelle verbindungen mit (alpha)-diazo-ss-ketoester- und sulfonsaeureester-einheiten, verfahren zu ihrer herstellung und deren verwendung |
| DE4014648A1 (de) * | 1990-05-08 | 1991-11-14 | Hoechst Ag | Positiv arbeitendes strahlungsempfindiches gemisch und strahlungsempfindliches aufzeichnungsmaterial fuer die belichtung mit duv-strahlung |
| JP3030672B2 (ja) * | 1991-06-18 | 2000-04-10 | 和光純薬工業株式会社 | 新規なレジスト材料及びパタ−ン形成方法 |
| US5945517A (en) * | 1996-07-24 | 1999-08-31 | Tokyo Ohka Kogyo Co., Ltd. | Chemical-sensitization photoresist composition |
| US5908730A (en) * | 1996-07-24 | 1999-06-01 | Tokyo Ohka Kogyo Co., Ltd. | Chemical-sensitization photoresist composition |
| US5866295A (en) * | 1997-03-07 | 1999-02-02 | Clariant Finance (Bvi) Limited | Photosensitive quinolone compounds and a process of preparation |
| US5876897A (en) * | 1997-03-07 | 1999-03-02 | Clariant Finance (Bvi) Limited | Positive photoresists containing novel photoactive compounds |
| KR100508699B1 (ko) * | 2001-08-09 | 2005-08-17 | 학교법인 한양학원 | Ａｆｍ 리소그래피용 아조 화합물 레지스트 |
| KR100620672B1 (ko) * | 2002-12-14 | 2006-09-13 | 주식회사 하이닉스반도체 | 포토레지스트 조성물 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3567453A (en) * | 1967-12-26 | 1971-03-02 | Eastman Kodak Co | Light sensitive compositions for photoresists and lithography |
| US3668197A (en) * | 1969-07-22 | 1972-06-06 | Merck & Co Inc | Esters and amides of (diazomethyl) phosphonic acid |
| GB1529552A (en) * | 1977-05-31 | 1978-10-25 | Hercules Inc | Photocrosslinkable polymers |
| US4207107A (en) * | 1978-08-23 | 1980-06-10 | Rca Corporation | Novel ortho-quinone diazide photoresist sensitizers |
| US4339522A (en) * | 1979-06-18 | 1982-07-13 | International Business Machines Corporation | Ultra-violet lithographic resist composition and process |
| DE3126627A1 (de) * | 1981-07-06 | 1983-01-20 | Hoechst Ag, 6000 Frankfurt | Polyvinylmethylphosphinsaeure, verfahren zu ihrer herstellung und ihre verwendung |
| US4522911A (en) * | 1983-06-28 | 1985-06-11 | International Business Machines Corporation | Deep ultra-violet lithographic resists with diazohomotetramic acid compounds |
-
1985
- 1985-03-28 US US06/717,254 patent/US4601969A/en not_active Expired - Lifetime
- 1985-12-24 JP JP60289539A patent/JPS61223837A/ja active Granted
-
1986
- 1986-01-08 CA CA000499173A patent/CA1221864A/en not_active Expired
- 1986-03-14 DE DE8686103438T patent/DE3662317D1/de not_active Expired
- 1986-03-14 EP EP86103438A patent/EP0195986B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0195986B1 (en) | 1989-03-08 |
| JPS61223837A (ja) | 1986-10-04 |
| EP0195986A2 (en) | 1986-10-01 |
| US4601969A (en) | 1986-07-22 |
| CA1221864A (en) | 1987-05-19 |
| DE3662317D1 (en) | 1989-04-13 |
| EP0195986A3 (en) | 1987-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |